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Cyclization of isoprenoid compounds

Communication 24. The possibility of stereospecific synthesis of the bicyclofarnesol system having cis- and trans-ring junctures

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The cyclization reaction of cis- and trans-1-(α-monocyclofarnesyl)-2-acetoxypropanes (IX) upon reaction with H2SO4 leads with good yield to 1-(cis-A/B-β-bicyclofarnesyl)-2-acetoxypropane (X) with an admixture (up to 20%) of theγ isomer (Xa). Upon carrying out this reaction with BF3 etherate the content of theγ-isomer in the mixture is increased to 50%.

  2. 2.

    Under analogous conditions cyclization of cis- and trans-1-(β-monocyclofarnesyl)-2-acetoxypropanes (XI) proceeds more complexly and cannot serve as a preparative method of obtaining the corresponding bicyclic systems of the trans-decalin series.

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Literature cited

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    G. E. Muntyan, E. I. Mortikova, V. A. Smit, A. V. Semenovskii & V. F. Kucherov

Authors
  1. G. E. Muntyan
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  2. E. I. Mortikova
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  3. V. A. Smit
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  4. A. V. Semenovskii
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  5. V. F. Kucherov
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Additional information

Translated from Izvestiya Akademli Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1816–1822, August, 1969.

The authors thank A. V. Kessenikh and I. P. Yakovlev for taking the NMR and m spectra.

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Muntyan, G.E., Mortikova, E.I., Smit, V.A. et al. Cyclization of isoprenoid compounds. Russ Chem Bull 18, 1678–1682 (1969). https://doi.org/10.1007/BF00906407

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  • DOI: https://doi.org/10.1007/BF00906407

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